App Engine Bulk Data Upload URLError: “Connection reset by peer”?

Look at your server logs. Are you getting a heap size exceeded or OutOfMemmory exception? This will happen on the local dev server if your upload is large because the dev server keeps the datastore in main memory.

The server will hang for a bit and then you'll get a connection reset. I've had the dev server run out of memory with as little as 10MB of datastore data, since it uses a lot of extra RAM to organize it and store metadata. You can increase the size of the heap using the -Xmx switch.

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